PtCl2-catalyzed cycloisomerizations of 5-En-1-yn-3-ol systems

Journal of the American Chemical Society

Volumn 126, Issue 28, 2004, Pages 8656-8657

  Harrak, Youssef ^a   Blaszykowski, Christophe ^a   Bernard, Matthieu ^a   Cariou, Kevin ^a   Mainetti, Emily ^a   Mouriès, Virginie ^a   Dhimane, Anne Lise ^a   Fensterbank, Louis ^a   Malacria, Max ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PLATINUM DERIVATIVE; ALKYNE; CYCLOPROPANE DERIVATIVE; KETONE; PLATINUM CHLORIDE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ISOMERIZATION; RING CLOSING METATHESIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; CHEMISTRY; ISOMERISM; SYNTHESIS;

ALKYNES; CATALYSIS; CYCLIZATION; CYCLOPROPANES; ISOMERISM; KETONES; MOLECULAR STRUCTURE; PLATINUM COMPOUNDS;

EID: 3242713858     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0474695     Document Type: Article

References (26)

1. For recent contributions, see: (a) Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104-9105.
2. (b) Trost, B. M.; Doherty, G. A. J. Am. Chem. Soc. 2000, 122, 3801-3810.
3. (c) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511-10520.
4. (d) Martín-Matute, B.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2003, 125, 5757-5768.
5. (e) Fürstner, A.; Stelzer, F.; Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863-11869.
6. (f) Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305-8314.
7. (g) Charruault, L.; Michelet, V.; Taras, R.; Gladiali, S.; Genêt, J.-P. Chem. Commun. 2004, 850-851.
8. (a) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813-834.
9. (b) Méndez, M.; Mamane, V.; Fürstner, A. Chemtracts-Org. Chem. 2003, 16, 397-425.
10. (c) Lloyd-Jones, G. C. Org. Biomol. Chem. 2003, 1, 215-236.
11. (d) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem. Eur. J. 2003, 9, 2627-2635.
12. Mainetti, E.; Mouriès, V.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. Angew. Chem., Int. Ed. 2002, 41, 2132-2135.
13. Cadran, N.; Cariou, K.; Hervé, G.; Aubert, C.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. J. Am. Chem. Soc. 2004, 126, 3408-3409.
14. Marion, F.; Coulomb, J.; Courillon, C.; Fensterbank, L.; Malacria, M. Org. Lett. 2004, 6, 1509-1511.
15. Formation of metathesis-type products from intermediates of type 2 has been proposed: (a) Trost, B. M.; Tanoury, G. H. J. Am. Chem. Soc. 1988, 110, 1636-1638.
16. (b) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704-3709.
17. For a pioneering report, see: Rautenstrauch, V. J. Org. Chem. 1984, 49, 950-952.
18. For a recent intermolecular version: Miki, K.; Ohe, K.; Uemura, S. J. Org. Chem. 2003, 68, 8505-8513.
19. This moderate yield of 6a is presumably attributable to the volatility of this material.
20. Other dienic isomers (15%) contaminated product 5.
21. One hypothesis is that due to orbital stereocontrol, the 1,2-migration is not a concerted process, so that a certain degree of positive charge (carbocation) stabilization is required at the propargylic position. This would take place in the case of tertiary substrates.
22. Kirschberg, T.; Mattay, J. J. Org. Chem. 1996, 61, 8885-8896.
23. For previous reports of similar 1,2-hydride shifts with heteroprecursors, see refs 1c and 1c.
24. An alternative mechanism for this process would involve a 1,2-hydride shift taking place on a bicyclic platinum carbene formed by a 5-endo-dig process. We thank one referee for this suggestion.
25. (a) Barberis, M.; Pérez-Prieto, J. Tetrahedron Lett. 2003, 44, 6683-6685.
26. (b) Galopin, C. C. Tetrahedron Lett. 2001, 42, 5589-5591.